


Drive-in Your Way

by Grace_28 (orphan_account)



Category: Supernatural
Genre: Blushing Castiel (Supernatural), Boys Being Boys, But Supernatural cast is evil :(, Charlie being supportive gay friend, Cool Dean Winchester, Cute Castiel (Supernatural), Don't tell them I wrote that, First Kisses, Fluff, Happy Ending, I Wish This Was Canon, M/M, Meg being supportive gay friend, Movies in 15 Minutes, No John Winchester, The Princess Bride References, Uh..., Very domestic, burgers & beer, economics class?
Language: English
Status: Completed
Published: 2020-03-07
Updated: 2020-03-22
Packaged: 2021-02-28 03:47:14
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 3
Words: 7,787
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/22997155
Author URL: https://archiveofourown.org/users/orphan_account/pseuds/Grace_28
Summary: Castiel has always been content with watching Dean Winchester from afar. But one thing leads to another and the next thing he knows, he has a supposed "date" with the man himself. How will he ever get through a movie with Dean if he can't even open his damn locker when Dean walks by?
Relationships: Castiel & Dean Winchester, Castiel/Dean Winchester
Comments: 1
Kudos: 33





	1. Chapter 1

**Author's Note:**

> Haha~ New story guys~
> 
> Decided to start a new one while I had a brain fart on Dammit Cas! No worries, a new chapter will come soon.
> 
> Till then: Enjoy this mini story!

Castiel sat down at his lunch table quietly as he watched the excited crowd of highschoolers enter the cafeteria. He was looking, specifically, for Dean Winchester and his posse. Dean was smiling as he took a tray from the stack and began to move down the aisle. Benjamin Lafitte stood next to him, playfully shoving him as they joked about God-knows-what. But, Castiel didn’t care for Benjamin Lafitte. He was much more interested in Dean Winchester.

Dean Winchester was handsome. Like…  _ extremely _ handsome. And smart. Definitely strong too. The size of his biceps and his thighs were proof of that. Dean was also very compassionate, which was something Castiel had quickly realized after his many visits to Sam Winchester in his economy class. It added on to his already irresistible charm. Sadly, other than that, Castiel had only encountered him several times in the hallways, yet the very sight of him made Castiel’s knees weaken.

“Darling!” Balthazar’s cheerful voice broke him out of his trance. Castiel looked up from his… sad excuse for lunch, and smiled at his friend.

“Hello, Balthazar,” he greeted. Balthazar plopped down in the seat next to him, placing a hand over his shoulder.

“Afternoon, darling. I heard your boy crush Winchester got a job down at the Singer garage. Wanna come check it out with me tonight?” Castiel opened his mouth to reply, but his own brother seemed to beat him to it.

“C’mon Balt. You can’t keep stealing my lil’ bro away from me,” Gabriel rolled his eyes. “Besides, Cassie has a date tonight.”

“Since when?” Castiel asked. He tilted his head in confusion, trying to remember any plans he might have made. Which should’ve popped up immediately since he’s never made any.

“Since now,” Gabriel huffed. Castiel drew his lips into a straight line, raising an eyebrow at his overprotective brother. “Why does Balt need you anyways? He can check out those cars on his own.”

“Gabriel, it’s just to see where Dean works.”

“Like he matters,” Gabriel pouted. “C’mon why not hang out with your big bro?”

“Maybe it’s because the last time you took him somewhere, it involved stripers in Las Vegas,” Charlie snorted as she took a seat across from Castiel. He smiled at the redhead, signing a small gesture of appreciation. Charlie just smiled back and took a bite of her apple.

“That’s not true!” Gabriel protested. Everybody stared at him, making him squirm uncomfortably. “Alright, maybe it is a little true, but there weren’t any stripers. They were hookers.”

“Like that was any better,” Balthazar shot back. “And I won’t even do anything to him. Maybe just push him into Dean’s arms or something while he’s half-naked.”

Castiel’s face burned with that possibility, and he quickly shook his head. “Absolutely not,” he said.

Charlie raised an eyebrow. “I say go for it. Maybe once you become friends with him, he’ll be the general I’m missing in Moondoor.”

“Hey! Why is nobody taking the big brother’s side?” Gabriel pouted.

“Your side includes hookers,” Balthazar deadpanned. “My side includes him actually talking to the love of his life.”

“For the last time, Dean’s not the love of my life,” Castiel hissed. He hunched over the table, covering his eyes with his hands.

“So you don’t want to fall into his arms while he’s half-naked?”

“Of course I do!” Dean? Hot and sweaty after working with a car? Wearing a simple white t-shirt that does nothing to hide his biceps or his sweat lines? Count him and a hundred other ladies in!

“Then?” 

“He would be uncomfortable,” Castiel said lamely. Everyone at his table did a collective eye roll. “Think about it. Dean’s working hard-”

“Hard?” Gabriel’s eyes bulged. Castiel sighed. Only his brother could have a perverted mind.

“Dean’s working diligently on a car, only to have a man pushed into his arms. His focus is ruined, and his job is tossed aside for a joke.” Castiel frowned. “If someone did that to me while I was volunteering at the library, I’d smack them.”

“Even if it was Dean?” Charlie asked. Castiel's mind helpfully created an illusion of Dean’s lips kissing the back of his neck, spooking him while Castiel was trying to put a book back. 

“Okay, maybe not smack him, but you know what I mean.” ‘Yeah, smack him on the lips,’ Castiel’s mind once again helpfully provided the illusion of Dean’s lips, which would be very soft and moist and- “Totally inappropriate.”

“I guess.” Balthazar sighed.

“Alright, I’ll go ask him then.”

“Wha- Charlie, no!” Castiel hissed. He attempted to grab her arm, only to miss and get gravy on his shirt. “Damn it.” He wasn’t quite sure which he was cursing about: his shirt or his crazy friend walking up to Dean Winchester.

The redhead sauntered over to the front of the cafeteria line and stopped right in front of Dean Winchester. They exchanged a few words before Charlie pointed in Castiel’s direction. As Dean turned to look, Castiel slid under the table.

Then Castiel heard Dean’s laugh, and his face burned with embarrassment. He quickly tried to come up with a method for calling the troll of the table and begging to become a permanent resident. He wondered if this was how table trolls became table trolls in the first place: from embarrassment.

“I’m back~” Charlie practically sang. Castiel rolled his eyes and continued to stay under the table. If Charlie was anything but a master technician, she was also cunning and sly. She probably brought poor Dean against his will.

“Go away, you stubbly, intelligent, backstabbing human being,” Castiel grit out. Jesus, if Dean Winchester saw him like this- all crouched under a table with gravy on his shirt- no, Castiel would sooner die.

“Relax, CJ. Dean isn’t with me,” Charlie said. Castiel could literally hear her grin. 

“Sup, buddy?” Dean’s magnificent voice appeared out of nowhere. Castiel looked at him for a split moment before shrieking and trying to jump up from underneath the table. He only succeeded in hitting his head against the edge of the table and hissing in pain.

“Dean’s with you,” Charlie finished. Castiel glared at her from under the table.

“Sorry, man,” Dean said as he looked mildly offended that Castiel screamed after looking at his face. “Are you alright?”

“Uh, yeah. I’m sorry,” Castiel frowned as he rubbed his head. “I didn’t- didn’t expect to see you here.”

“Yeah, uh, I wouldn’t either,” Dean laughed. Castiel felt his entire body practically preen at the closeness of Dean Winchester. “Need help getting up?”

“N-no, I’m fine. Thank you, Dean,” Castiel mumbled. He slowly got back into his chair, ignoring the stare of every person in the cafeteria. His ears burned with embarrassment.

“Alright, suit yourself,” Dean shrugged. “Scoot over Gabe.”

“Sure Deano!”  _ Well _ Gabriel sure does seem supportive now.  _ What happened to strippers in Las Vegas? _

Castiel shot his older brother a glare as Dean Winchester took a seat next to him. Gabriel only winked back before Dean sent him the most charming smile Castiel has ever seen. Castiel knew he practically had heart eyes.

“You got some gravy on your shirt, man,” Dean pointed out. It wasn’t in a mocking way or anything, but the realization that Dean actually  _ noticed _ made Castiel’s ears burn with embarrassment.

“Sorry,” he muttered. Dean frowned.

“Well, uh, Charlie told me that you guys were planning to go to my Uncle Bobby’s garage,” Dean said. “It’s a pretty cool place, and we’re hosting this drive-in movie tomorrow night. I can sneak you in for free as an apology for scaring you, CJ.”

“Oh, uh, that’s not really his name,” Charlie helpfully interrupted him. “Sorry, that was my nickname for Castiel here.”

“That’s a pretty cool name. Jewish or Chrisitan?” Dean asked.

“Uh, Chrisitan,” Castiel mumbled. Dean grinned.

“Alright, then I’ll get you in for free, Cas.” Castiel’s heart actually stopped for a full thirty seconds. And then it was beating like a drum at a music festival. He knew his face was entirely red now, and he wasn’t sure whether or not he was angry at Charlie anymore. Castiel was officially in love with Dean’s nickname.

“O-okay,” Castiel mumbled instead.

“See you guys around,” Dean waved. He stood up and began walking back to Benjamin Lafitte. The moment he sat down with his friends, Castiel immediately gasped for air and slammed his face into the table. He banged it several times before Gabriel placed a pillow in between his head and the table.

“Why?” Castiel groaned. “Just end me now.”

“Darling you can’t just kill yourself after your boy crush asked you out on a date.”

“It’s not a date…” Castiel pouted as he sat back up. 

“What was it then?”

“Dean apologizing and offering me compensation for scaring me under the table!”

“Mhmm, well, I know for a fact that Deano never offered anybody a discount for his drive-in movies,” Gabriel said. His brother raised an eyebrow in Castiel’s direction, as to challenge him to retort to that.

“He-he could just feel  _ bad _ about scaring me.”

“CJ, Dean has shoved a line of people out of the way for pie. People who have flown several feet and crashed into walls. He’s never given a single discount to any of those poor people,” Charlie said. “And he didn’t just offer you a discount. He offered you a  _ free _ admission. I would totally approve if you marry him.”

“Charlie!” Castiel’s was probably so red, he looked as red as a person who’s been forced into the Spanish Tomato Festival. For a split second, he imagined himself there, standing next to Dean-frickin’-Winchester, his face buried in the crook of Dean’s leather jacket. As his frickin’ boyfriend nonetheless. And he knew that that thought probably turned him into a brighter shade of pink.

“Me too. Deano’s a good kid. I can hear the bells already- oh, Cassie I’m so proud.” Was Gabriel actually tearing up? Holy shit.

“Gabriel!”

“I must admit darling, Dean’s a perfect candidate for you.” Balthazar seemed totally cool with the idea of Castiel marrying Dean- his head was leaned back a little as he took a sip of his apple juice as if it was wine, his carton held at the bottom by his index and his middle finger. Castiel groaned in exasperation. 

“Not you too, Balthazar! Why couldn’t he just be apologetic?”

“Because he’s been apologetic hundreds of times without giving anyone a free ticket into the Singer’s garage! He knows what’ll come and bite his ass if he gets caught!” Charlie hissed. Castiel stared at her.  _ Bite his ass? _ Was Dean from an abusive home? “He’s risking a lot for you, Cassie. I need to come over to your house and give you a makeover.”

“Make up?” Castiel scrunched up his nose. She sighed.

“No, I mean, style your clothes and hair,” Charlie smiled. “It’ll be so perfect Dean will  _ have _ to kiss you at the drive-in!”

“Charlie!” Castiel blushed. He stood up and threw his sandwich at her. Charlie just slapped it midair and grinned. She practically pranced away when the bell rang and Castiel was left miserably thinking about how many different ways he could mess up that night.

~~~

“Dean, brother, you look like you’d seen a ghost,” Benny remarked. Dean just nodded and took a seat across from him. He wasn’t quite sure what he’d just experienced. Yeah, he just took the biggest frickin’ courage leap he’s ever taken in his damn life, but did he regret it? No. Castiel- Cas, was an absolute cute, smart, and handsome angel, and Dean would never regret talking to him in his life.

“An angel, actually,” Dean muttered. He handed his apple to Sammy, who was pleased with the idea of more food. Sammy quickly took a large bite out of it, only pausing his chewing to tell Dean ‘thank you’.

“So you finally talked to Clarence huh?” Meg asked as she slid next to him. “You got a date, Deano?”

Dean shook his head. “I don’t think so. Cas seemed dismissive of the idea.”

“Nah, brother, just look at him.” Benny pointed in the direction of Cas’s table. Cas was sitting there, with his face entirely red. His friends seemed to be teasing him about something, and Dean found that he was somewhat pleased. It was a wonderful feeling to think that someone was blushing because of him. “He’s so bloody red.”

“Yeah,” Dean said softly. He turned back to Benny with a big smile. “I asked him to go to the drive-in.”

“What? No way!” Benny grinned back. He clapped Dean’s shoulder harshly. “Congrats brother!”

Dean winced. Jesus- “You say that as if we were dating.” 

“I know you wish you were, Deano~” Meg winked dramatically. She just laughed as Dean’s facial expression turned sour.

“Oh shut up, Meg!” Dean hissed. He thought about it for a moment though: seeing Cas sitting here, next to him, just laughing at a stupid joke Dean would make or explaining a subject Sammy would have to take as he grew older. The idea of Cas sitting next to him and occasionally snuggling up against his shoulder… Well, obviously, he would sometimes sit at Cas’s table to hang out with his friends. They would get teased for holding hands underneath the table- since Dean was right-handed and Cas was left-handed- and smiling like an old married couple who have seen too much shit. It wouldn’t be too bad- no scratch that, it would be freakin’ awesome if Cas was with him. Dean scratched the back of his neck. “But it would be pretty awesome to have him sitting here with us.”

“Dean, you like Castiel?” Sammy asked. Dean turned to him in shock, blinking in surprise. None of them had mentioned his name, yet Sammy seemed oddly invested in the dude.

“How do you even know his name?” Dean asked. His brother shrugged.

“He’s in my economics class. Castiel is pretty cool. I definitely approve if you’re going to start dating him.” Sammy smiled. Dean sighed, he totally forgot about that. Well, not about the economics class, but rather the fact that Sam was in the room whenever Dean strolled by. More than half of the time, Dean’s eyes were trained on the cute bedhead that always seemed like he had “fun” the night before. Before Dean’s brain could even go in that direction, Sammy added, “I could really use his help for the homework assignments.”

“Sam!” Dean scolded. “Well, he probably won’t even go tomorrow. I acted like a total douche.”

“Not a surprise,” Meg smirked. Dean sent her a poker face.

“Seriously, I scared him and then told him that he could go in for  _ free _ ,” Dean groaned. Then he sat upright. Oh shit, Bobby would kill him for suddenly saying something like that! What is Cas actually does come and Bobby sees him coming in? “Forget acting like a douche, Bobby’ll kill me!”

“I’m surprised you even offered a movie for free,” Benny snorted. Dean tried to interrupt, only to realize that Benny wasn’t finished yet. “Remember that time when you threw a poor man aside for that apple pie?”

Dean groaned. “Don’t remind me of that time. I apologized to him ten times. And the pie was frickin’ worth it.” All three of them laughed. “But Cas is different from that dude.”

“How?” Meg challenged. Benny and Sammy stared at him in interest, and Dean wasn’t quite sure how to explain it.

Cas was… he was compassionate. And he was kind and smart. He was fair to everyone, and he stood up for anyone who was even getting the slightest bit bothered. And Cas always had that look on his face where he’s focusing to see an alternative where everyone is included in any activity, whether it was group projects or sport festivals. Cas was amazing as a person, but that was all that he was. Though Dean didn’t really know him that well, he was certain that Cas has made mistakes. After all, how could he avoid making mistakes? 

That’s probably what drawed Cas to Dean in the beginning. His imperfect perfection. The way his smile is slightly crooked when one joke is particularly funny. Or the way that he keeps fumbling with his locker combination. Or the way that he stumbles over his feet and practically headbutts into a table. “He’s average.” Dean wouldn’t want him any other way.

“Oh, Deano, you say it like it’s a marvelous thing,” Meg said before she threw her head back and snickered. “If that was your only interest, there are billions of other humans who fit your interests.”

“No, what I mean is: Cas is average in a good way.” Dean sighed. He rested his cheek on his hand, smiling to himself as he played with the plastic knife he’d always described as “stupid”. (It never frickin’ works! He couldn’t frickin’ cut any of his lunch with that piece of shit) “Cas is hot, kind, and really frickin’ smart. But, he’s human, and I know he makes mistakes. He ain’t perfect, but he is… y’know, perfect.”

Meg cooed at his small explanation. “Oh shut it, Meg,” Dean hissed.

“Dean, I think you really like him. Like, like-like him,” Sammy said. He was grinning like an idiot, his eyes twinkling, and his mouth stuffed with greasy food from God-knows-where. Dean rolled his eyes. “I’m already planning to accept his question to bless you two.”

“Don’t be a bitch. I’m too busy for that.”

“Yeah, which is what you said before you started working at Bobby’s,” Sammy shot back. Dean narrowed his eyes. “And see how that turned out?”

“You’re on thin fuckin’ ice,” Dean muttered. Then he took a bite from his cafeteria pizza, frowning a little at the bland taste. Meg and Benny turned to each other, winking dramatically across the table. “What?”

“How would you like us to help you hook up with Clarence?” Meg asked idly. 

“What? No!”

“Think about it: We’ll help you dress nice-”

“My shirts are nice!”

“Not if it’s brownish plaid Dean Winchester! Good heavens, that shirt was atrocious!” Dean scowled.

“Okay, fine, but my shirts aren’t as bad as Benny’s,” Dean smirked. Benny let out a gasp or betrayal.

“Brother, if my shirts are bad, yours are horrible!”

“Anyways, where was I? Oh yes, nice clothes, romantic lines, and- food is a must! Bring chicken, beer, and pie!” Meg clapped her hands in glee. “Alright, Winchester. Get ready to get your filthy hands all over that fabulous unicorn!”

“Meg!” Dean groaned in embarrassment when other people looked their way. He covered his face with his hands, no longer even looking at her. “Seriously?”

“Hey, if lil’ Sammy needs that tutor as much as my brother needs a boyfriend, then I’m ready to do anythin’,” Benny said as he winked. Dean just rolled his eyes again and turned away.

“I’m leaving. Goodbye~” Dean waved his hand dismissively as he stood up and left the cafeteria- leaving his friends and his brother to his tray of odd-tasting cafeteria pizza. He absolutely refused to be made fun of for thinking of Castiel-frickin’-Novak in a certain way.


	2. Chapter 2

“You what?!” Bobby snapped when Dean told him what he offered to Cas. Dean winced. He knows. He knows that noney was always tight for the old couple. Especially because they’re in the small city of Lawrence, Kansas. Dean should’ve thought the whole thing through. Maybe Bobby would take money out of his salary for it. Sorry, Sammy. Looks like you’ll eat cereal for dinner for a couple of days. Dean looked down at the floor, sighing. “I know, I’m sorry. I should've thought more about how it would affect you and Ellen. I’m willing to just pay for his ticket at the drive-in-”

“Shut your trap, boy, I ain’t talkin’ bout the drive-in. I couldn’t give less of a damn,” Bobby said as he barked out a laugh. Dean stared at him, open-mouthed and completely in shock. Then what…? Why was Bobby pissed? “Listen, Dean, you’ve never even made a scratch on any customer's car. I wouldn’t bat an eye if you failed all your classes.”

“But what I’ve done was irresponsible-”

“It doesn’t matter, Dean. Last time I checked, you’ve never done this before- not even for that poor man you threw out the door for pie- and I don’t give a damn about one frickin’ admission.”

“But-”

“What I care about is the fact that you acted like a frickin’ douchebag the whole time! No empathy, no jokes, no nothing. It’s like you lost yer charm or somethin’!” Bobby frowned, passing him a beer from across the table. He sat back down though he was still obviously distressed about the whole thing. Dean expected yelling, lots of it, about messing up business and all he’s receiving is a taunt on what he said to Cas. It’s like- it’s like- “Kid, yer happiness is worth more than two bucks. Believe me. And taking a day off won’t kill ya either.”

“Oh.” Dean was stunned. He had absolutely no idea what to say. He’d always thought that he was just a worker in Bobby’s eyes- just one kid who recklessly fixes cars from time to time. But to think that Bobby actually cared about him… wow, he couldn’t have ever expected that.

“Besides, I’m gettin’ sick and tired of seein’ ya face dirty every day,” Bobby snickered. “You better apologize damn right, boy,” Bobby warned menacingly. “Or else ‘m cuttin’ yer paycheck.”

“What?” Dean asked, shocked by the sudden change in Bobby’s behaviour. Bobby raised an eyebrow as he brought a bottle of beer to his mouth. Dean shut his mouth. It was never good to argue with a man who is like his father and is his boss. He’d never make that mistake, no siree!

“Treat him to dinner or somethin’. Bake him a pie, who cares? All I want to see is you smiling like an idiot tonight and workin’ like normal tomorrow. Understand?”

“...yes, sir!”

“Good. Now go get ready. I’ll ask Ellen to help out tonight.” Dean could only wordlessly nod along to whatever Bobby was saying. He still couldn’t believe it. It was okay for him to grant Cas a free ticket. And his only parental figure allowed him to take time off of work to apologize to Cas- a man he’s never even met before. Dean walked out the front door, still surprised by his uncle’s reaction. 

But, he knew he had bigger problems now.

Like… What would he even make for Cas? Since it wasn’t a “date”, he obviously couldn’t try too hard. He couldn’t risk being made fun of for looking like one of those kids from that movie Grease. And he also couldn’t half-ass it since it’s supposed to be an apology. Dammit, is there something called an apology cake? Or pie? Or a sandwich? Or- burgers! Dean could definitely make some burgers and put them in his bag or something.

“Move!” he hollered as he raced down the road. A car honked at him, but Dean continued running down the road. He absolutely refused to forget about this idea of his.

He got in his car and raced like a jet to the nearest supermarket. He grabbed meat, buns, lettuce, cheese, and, most importantly, bacon. Dean paid and quickly raced home. He prepared everything perfectly, knowing that there was no time to lose. Just as the patties were getting off the grill, Meg and Benny barged in.

“Dean!” Benny yelled.

“In here!” Dean called from the kitchen. He expertly placed the patty on top of the bottom bun, placing two bacon strips on top of it. Then he added the piece of lettuce before topping it with the top bun.

“Oh Deano, you didn’t need to make this for us. We’re doing this out of generosity.” Dean turned around to see a smirking Meg and a confused Benny. Dean rolled his eyes.

“Glad you caught on. These ain’t for you too.”

“For Castiel?” Benny asked. Dean nodded.

“I talked to Bobby and he said I should apologize in some way. I decided on apology burgers so…”

“Glad you took my advice then. All we need is beer and a touch of romance and you’re all set to go,” Meg joked. Dean rolled his eyes again as he prepared his own burger.

“I’m planning to bring a pie. We have school tomorrow, Meg,” Dean reminded her. She clicked her tongue.

“Right, forgot about that stupid son of a bitch,” Meg sighed. “Where’s Sam?”

“Upstairs. Told ‘im he could play games on my computer.”

“Alright, well get yer ass upstairs when yer pie’s in the oven, brother. We’ll go hang out with Sam.” Then Benny promptly turned and followed Meg upstairs. Dean just smiled as he continued to grill his own patty.

When he finished, he went upstairs himself, really confused on what they might have wanted. He opened the door to his bedroom, mentally preparing himself for the worst of the worst. “Hey, guys. I’m done.”

He was greeted with the sight of Meg braiding Sam’s hair and Benny playing on his Xbox. “Oh, hey, Dean. Meg was just telling me about your date tonight. I really-”

“What?” Dean pulled at his hair. “Sammy! I don’t have a date, don’t listen to Meg.”

“So you weren’t making burgers for Castiel and planning to eat with him at the drive-in?”

“Okay, I was, but that’s different,” Dean said, though he struggled to explain how. He made burgers, made pie, and was going to eat with Cas for dinner. In other situations, this would sound like a date night.

And suddenly he thought of a scenario if they did start dating. They would lay on a blanket, just talking and chatting after they’ve eaten dinner together. Cas would say that he brought beer and he would offer to grab one for Dean. Dean would pull him in for a kiss before Cas would stand up. When Cas disappeared into the trunk of the Impala, Dean would look up at the stars, trying to find constellations he recognized. When Cas came back, Dean would report his findings, and then Cas would make stupid little stories about how each star came to be.

“-Dean.” His friends and his brother looked at him expectantly.

“Sorry, what?” Dean cleared his throat. Benny sighed.

“Nothing, we were just talking about your sense of style,” Meg interrupted. “Sam was being a doll and telling us what you most likely looked the best in.”

“For what?”

“Tonight, duh,” Sammy sassed. Dean sighed, taking a swing of Benny’s beer. Benny hissed upon the loss of his best mate, which Dean just ignored.

“Alright, hand it over,” Dean said as he flexed his hands. Sammy grinned, handing him a pile of clothes. Dean sighed again.

He took off his shirt, earning wolf whistles from Meg. He rolled his eyes again and changed as fast as possible. Dean then pulled the leather jacket around him.

“How do I look?” 

“I think you look great, Dean.”

“Sammy, you’re just saying that because you were the one who chose the clothes,” Meg smiled as she said it. Sammy pouted and Dean took it to his heart to help him out a little.

“Hey hey, Sammy’s just expressing his opinion. I love it,” Dean fired back. Meg smirked.

“Oh yeah? Then wear it, princess.”

“What?”

“Yeah! Dean, you should totally wear it tonight.”

“Like tonight tonight?” Dean asked, completely baffled.

“No, brother, tomorrow tonight,” Benny sassed. He rolled his eyes, gesturing wildly at his clothes. “You said you loved it.”

“Yeah, but doesn’t I mean I will wear it!” Dean snapped. Sammy looked up at him sadly. “Oh, come on!”

“Please Dean? For me?”

“Oh you think every time you say that-”

“Dean...”

“Jesus! Fine!” Dean sighed loudly. “I’ll wear it. And not because you gave me your sick puppy eyes.”

Sammy just grinned, looking back at Meg and Benny. As if to tell them ‘I told you so’. Dean frowned. “Wait a minute!”

“Too late! You’ve said you would wear it,” Sammy taunted.

“Before when you tricked me!”

“Your word is your word!” Meg shouted as she laughed maniacally to herself. Dean just rolled his eyes.

“Whatever, I don’t have time to change anyways. It’s going to start in an hour and I need to clean up Baby.” He refused to listen to all of Meg and Benny's whooping as he walked out the door. Dean could only pray that he looked presentable and they were not just pulling his leg. 

  
~~~  


“Wassup bitches?!” Charlie hollered as she stomped into Castiel’s dorm room. She was holding this massive black gym bag, and Castiel was actually surprised she showed up. Charlie threw the bag down, immediately jumping up and down and squealing. Castiel only stared at her for several moments before sighing and standing up. When she gets like this… Castiel should just get this over with.

“Hello, Charlie,” he greeted quietly. He made sure to shut down his computer and unplug his earphones. “Are you still insisting upon ‘changing my clothes’ and ‘messing up my hair’?”

“Of course! Cassie, you’re about to get a husband! As your honorary best-”

“Charlie! Dean and I aren’t getting married!” Castiel rubbed his temple with his fingers. “This isn’t even a date.”

“Mhmm, sure, Cassie.”

Castiel just sighed. She bent over and grabbed several things from the bag as Castiel could only watch in horror. “Why are there so many clothes?”

“Okay, hear this: I took these from my brothers and they all have horrible tastes. So I grabbed some of their wardrobe and brought it all here. We have enough time to try every possible combination.”

“Charlie-”

“No buts! Just try this on!” Charlie shoved a red plaid shirt and a pair of black jeans into his arms. She shooed him into his bathroom. Castiel could only do as she asked, though he did do it grudgingly. He pulled his grey shirt over his head and fumbled with the buttons a bit. Then he slipped into the jeans as fast as possible, trying not to cringe when it got stuck at his thighs.

“Is this okay?” Castiel asked when he finished changing. Charlie stared at him for a good five seconds before she shook her head and shoved a Metallica shirt into his arms.

“Go.” Castiel sighed and returned to his bathroom again.

They probably repeated this fifteen more times until Charlie finally squealed in joy. Castiel had to plug his ears with a slight smile. He was exhausted from the constant look of rejection. “Cassie that’s perfect!”

“Yes, I, uh, realized when you started screaming.” Castiel chuckled to himself, though his relief was short. He barely had the chance to look at what he was even wearing before Charlie pulled him back into his spinning chair and pulled out a hair brush and a blow dryer. 

Castiel wasn’t quite sure what happened. All he knew was that there was hair brushing and hair pulling. And by “pulling”, he means “yanking his hair from the frickin’ roots”. It was a very painful fifteen minute process. Even though he had voiced this by groaning and glaring at her, Charlie didn’t seem to care about his pain, humming along to a nonexistent tune. By the time she was done, Castiel knew he lost a lot of hair strands and was already planning to ask her for a wig. At her expense, of course. 

“And voila!” Charlie grinned. She grabbed him up from his chair by the arm, tugging him towards the bathroom. Castiel had grown quite familiar with the bathroom now- had apparently become besties for the night. But, when he looked into the mirror, he had to admit Charlie did a good job.

He looked about the same, just with slightly messier hair and a baby blue sweatshirt. Charlie told him to shave, mentally prepare himself, and then leave for the drive-in movie before disappearing. Castiel didn’t even get to say thank you. He knew what her response would be though: “Yeah, yeah, just make me your maid of honor or something.”

As he drove there, he picked out this pack of beer, which he hoped Dean didn’t mind. If he expected Castiel to come anyways. When he arrived at the drive in, he wasn’t quite sure what he was supposed to look for. Everyone was just sitting on the floor, eating or chewing something as they watched the ads on the large white screen. He was quite lost. Where could he go to pay…?

And where was Dean?

Castiel let his eyes wander around the dark field, only for his eyes to fall on a certain Winchester. The man was wearing a leather jacket and his hair was styled in a classic way. It suited him terribly well. Castiel’s mouth formed a silent ‘o’ and all he could think about was how stupidly whipped he was for Dean Winchester. Of course, the assbutt had to just see him at that damn moment and begin to make his way over. 

God dammit Charlie, how the hell was Castiel supposed to prepare himself for this?

**Notes for the Chapter:**

> Hmmmm~~~ do any of you guys have friends like Charlie? Like people who just desperately want you to get married??? I'm just curious as to whether it is an actual thing or not...
> 
> Lemme know in the comments! :D


	3. Chapter 3

“Hey, Cas,” Dean greeted with a small wave. Castiel sighed out of happiness when he heard the nickname again. He had no idea why the nickname bothered him so much, and he had no idea how a simple wave could make him seem even more handsome. “Glad you could make it.”

“Wouldn’t miss it,” Castiel muttered. He coughed and looked around for help, preferably from Charlie and not from Gabriel’s ‘hookers’ or Balthazar’s possibly flirtatious ideas. “I brought beer?”

As if he had just lit up Dean’s whole world, Dean grinned at him. “Great! I saved you a spot.”

A spot? For what? And Castiel still had no idea where to even go to pay for the movie. “Dean.”

“Yeah?”

“Don’t I need to pay?” Castiel asked as he narrowed his eyes. “I wouldn’t want you to get yelled at for ‘sneaking me in’. I don’t mind paying, really.”

“Nah, I talked to Bobby about it,” Dean replied thoughtfully. His cheeks seemed to have turned slightly pink, though Castiel couldn’t really tell. Dean shrugged, smiling softer. Castiel instantly understood that Dean truly respected the man, and he kind of wanted to meet him. “He seemed cool with it.”

“Are you sure?”

“Yeah, in fact, he said that he wouldn’t have cared if I failed all my classes.” Castiel stifled a chuckle. Dean could never be capable of doing such a thing. He was too intelligent to allow that to happen. Dean sent him an odd look.

“What?”

“Nothing, you just look nice when you smile,” Dean said. Then, he definitely turned bright pink as he cleared his throat. Castiel tried to make sure that his mouth wasn’t gaping from the sudden compliment. “Sorry, uh, let’s go.”

Castiel nodded, stepping in beat with Dean. Dean seemed to be going at a pretty quick pace, and Castiel realized that he was probably embarrassed to not receive a compliment back. He cleared his throat, reaching out to tug on his leather jacket. “Uh, Dean, you look really nice when you smile too.”

“Th-thanks.” Dean finally gestured to a stunning black car. “This is my Baby. She’s a 1967 one of a kind.”

“She’s beautiful…” Castiel said in awe. Dean blushed, and with a slight nod, allowed Castiel to walk over slowly. He brushed his hand against the car’s exterior with a wide smile as he did so. He vaguely remembered looking through his brother's magazine and seeing this same car. “Did you fix her up yourself?”

“Yeah, uh, I got it from my dad when he couldn’t fix it. Said that if I could, she was mine,” Dean grinned. Castiel grinned back. “Why? You like her?”

“Yes. I was always a fan of classic cars. Correct me if I’m wrong, but I heard that the Batmobile was modeled after her?” Castiel asked unsurely. He believed that Gabriel mentioned it once to him after watching a movie about the superhero.

“Really?” When Castiel nodded, Dean chuckled, forcing Castiel blush. “Awesome. Here I was thinking that I was going to share a beer with a person who doesn’t like cars.”

Castiel smiled. “I’m glad you aren’t. Thank you for inviting me by the way. I’ve never been to one.”

“Never?” Dean gasped. Castiel nodded.

“I never understood the appeal of watching a movie or sitting in your car and watching a movie.”

“Cas-” Castiel sighed at the name again, his chest feeling slightly lighter than it had been all night- “well, aren’t you lucky? Your first movie’s ‘The Princess Bride’!”

Castiel tilted his head. “Is the name supposed to have some sense of appeal?”

“Of course! It’s a classic, just like my Baby.” Dean smiled. “C’mon, it’s starting.”

Dean gestured towards his car, and he realized that there was a huge blanket inside the car. It was red plaid- which was cute- and there was this brown bag sitting on top of it. “Uh, Dean, what is this?” Castiel asked before he stepped inside.

Dean’s face flushed. “I-I thought I could make you some burgers since the movie plays around dinnertime.”

“Oh.” Dean just moved the bag out of the way so Castiel could sit down, and then he distributed the burgers. “Thank you, Dean.”

There was a few seconds of silence before Dean spoke up. “Yeah, no prob. It wasn’t that difficult to make so…”

“It doesn’t mean that your action isn’t appreciated,” Castiel muttered. “So thank you.”

Dean, instead of replying, took a big bite out of his own burger. Castiel mirrored his action, though the amount of flavor in his burger resulted in some sinful noises. He chewed, savoring the taste, before smiling widely. “S-sorry, it’s just- your burgers are really amazing.”

Dean blushed before taking a bite out of his own burger. The shade complimented him very nicely, well, more specifically the freckles that decorated his cheeks. “You’re amazing.”

Dean choked on his burger and his eyes bulged. He hit his chest several times. Castiel tilted his head in confusion. When he realized what he said and blushed himself. “Sorry! I meant- I meant that you’re beautiful- ack! I mean that your cooking style is beautiful! I mean you’re really good at cooking or grilling- or whatever!”

Dean just stared at him before laughing. Castiel wondered if it was possible to die from blushing too much. He’d have to research it at home. “Glad you like it, Cas.”

Castiel’s heart fluttered at the nickname again. Castiel sputtered unintelligently again and just handed Dean a beer with his shaky hands. He accepted it graciously, popping the lid open before turning back to the screen. Castiel followed his example.

They only lasted two minutes before Dean started to shuffle around. When Castiel turned to look, Dean had taken off his jacket and offered it to Castiel. He tilted his head in confusion. “What?”

“I noticed that you were shivering. Your sweater isn’t doing much.”

Castiel nodded, playing with the hem of his sweater with fingers. “Yeah, I should’ve told Charlie that before she forced this on me and left.”

“You too huh? Meg and Benny did that to me right before you got here,” Dean confessed. Castiel froze. Did he just say that his friends helped him get ready for this?

“Oh.” Castiel simply couldn’t understand him. 

“Anyways, here. You should cover up before you get sick,” Dean smiled. Castiel nodded.

“Thank you, Dean.” Castiel gracefully took the jacket and shuffled around to put the leather jacket on. The moment he was comfortable, he relaxed.

The jacket smelled like Dean. It was clearly scented with apple pies and the burger he was eating. But if he paid closer attention to it, Castiel could smell the slight tinge of beer. The smell of the jacket was intoxicatingly comforting. “You feel better?”

“Yeah.” Castiel smiled at him. Then he snuggled back into the jacket, covering half of his face with it. He turned his attention back to the screen, confused when he realized that the girl was getting married. Castiel wasn’t even sure what had gotten to this point. And to that jerk too?

Castiel frowned. He refused to watch anymore. So, instead, he turned his head to watch Dean. Dean seemed entirely mesmerized by the screen; his green eyes were sparkling with the reflection of the show in his eyes. Castiel took notes on the way that Dean’s facial features changed with every emotion he was feeling. When he was annoyed, his eyes narrowed into a tiny slit. When he was surprised, his eyes widened a little and his mouth dropped. But, Castiel’s favorite appeared when Dean started to chuckle to himself because of something the characters said.

Dean was a very interesting person, that’s for sure.

“Cas, you okay?” Dean’s voice snapped him out of his trance. Castiel blushed upon realizing that he was caught staring.

“Yes. Sorry,” Castiel said. He quickly thought up the most plausible excuse. “I just realized that we have school tomorrow.”

Dean stared at him in shock before laughing. It was like music to his ears. “God, this is why I love you, Cas. You remember the most random thing during a movie.”

Castiel’s eyes widened as his brain registered this new piece of information that he learned. His brain picked at the comment for several long moments. “What?” he unintelligently screeched. Dean raised an eyebrow.

“What?” Dean asked.

“You love me?” Castiel said in astonishment.  
~~

“I just realized that we have school tomorrow,” Cas pouted, staring at his beer blankly. Dean blinked before laughing to himself. Cas could be so cute sometimes.

“God, this is why I love you, Cas. You remember the most random thing during a movie,” Dean commented as he grinned. Cas didn’t reply and just stared at him with his eyes wide and mouth open.

“What?” Cas screeched aloud. Dean raised his eyebrow.

“What?” he repeated back. Cas exhaled, staring at him.

“You love me?” Alarms went off in his mind, blaring like a train’s horn. What? How the fuck did he know? Cas seemed quite shocked. 

“Wh-what?” Dean asked as he blushed madly. How did Cas guess? How could Cas have guessed? God, what did Cas think? Was he disgusted? Was he in awe? Was he-

“Y-you just told me,” Cas muttered. “You-you said that you loved me. ‘Cause I-I remembered school. You said you-you love me.”

“I- I did?” Dean asked stupidly. Of course he fuckin’- of course he had to blow his frickin’ cover! God, he’s such an idiot! What the hell?! “Sorry,” he mumbled.

“What? Why?”

“‘Cause now you have to find a reason to reject me without ‘hurting my feelings’.” He wasn’t being fair to Cas. God, he just had to be a douchebag and ruin the movie for him too. Cas came for the frickin’ movie! Goddamnit, Dean.

“What? Why?” Cas looked really confused now. Dean frowned.

“Y’know, cause you don’t like me and stuff. I read books and it usually ends like that. And I- I made you uncomfortable and stuff.” He was now so nervous for Cas’s answer that he was playing with his shirt. Dean already had a feeling what the answer was: a big, fatass, frickin’ N.O.

“What? Dean, that’s absurd!” Cas nearly shouted. Dean jumped at the sudden ferocity. The person in the next car hushed him. He shot an apologetic glance at her. Cas turned back to him in shock. “I’m not going to reject you- of course I’m not!”

“What? Why?”

“Maybe because I literally wanted to go on a date with you the moment I saw you at school. Or maybe because I was so worried about the movie with you that I spent hours in the bathroom just changing clothes. Or maybe because you’re literally right here, offering me your jacket, and then feeding me burgers and telling me that you love me!”

Dean blinked. “So does that mean…”

“Yes! That’s a ‘yes’!” Cas sighed in exasperation. Dean blinked again.

“Oh.” Good grief, was he a frickin’ drone? Dean stared into Cas’s eyes, which now held the intensity and fierceness of a deadly storm in the sea, yet held the compassion and kindness that the clouds in the sky represented. Everything was so confusing. How could Cas like him back? It just didn’t make any sense. He had thought about it long and hard for many hours as he waited for Cas to come into the drive-in. And suddenly, only one thing became clear to him. He wanted to kiss Cas a whole frickin' lot. “Can I kiss you?”

Cas’s eyes widened. “Please.”

Dean sighed a breath of relief, swiftly moving in; he cupped Cas’s face, tilting his head a little to the left, and then gently pressed his lips against Cas’s lips. They were soft, yet firm. They tasted a bit like beer and the bacon burger Dean had made. Dean couldn’t help but smile as they both slowly moved their lips.

“God, Cas, you have no idea how long I’ve wanted to do that for,” Dean muttered when they broke apart to breathe. Dean moved back in, relishing in the way their teeth scraped together with the intensity of their kiss. They just sat like that, simply kissing while Buttercup and Westley kissed at their wedding.

As he kissed Castiel, it suddenly struck Dean that he, one day, wanted to marry Cas. He could see it now. They’d have a wedding just like Buttercup and Westley did in memory of their first kiss. Or have one with just themselves.

“I’m beginning to have one,” Cas muttered back. When they broke apart for real, Dean took pride in the way that Cas’s lips seemed a bit more swollen.

“Hm?” Dean questioned. Cas had one what?

“An idea,” Cas hummed. He seemed a bit dazed, and Dean wanted to just stay here forever: sitting comfortably in Baby with Cas and kissing him till he’s dazed. Then, Cas suddenly laughed.

“What?” Dean couldn’t resist his curiosity.

“I just realized that I didn’t get to watch any part of the movie,” Cas mumbled cutely. Dean chuckled, brushing part of Cas’s hair out of his face.

“Then we could rewatch it sometime. Okay?” Dean offered. Cas smiled. “Can we just stay like this right now?”

“Okay,” Cas confirmed. He placed his forehead against Dean’s shoulder sleepily. He mumbled, “Love you too.”

Dean beamed. He decided to be a bit more bold than usual and kissed the top of Cas’s head.

**Notes for the Chapter:**

> Hello! How was your day? Hopefully you guys aren't as bored out of my mind as I am. I kinda wish my fellow writers out there would write faster XD or somebody introduces an awesome fic...
> 
> Do you have any recommendations?
> 
> Oh, and please stay safe and remain healthy! <3


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